The Obstacle Is the Way: Summary & Review

the obstacle is the way book cover

The Obstacle Is the Way (2014) takes inspiration from ancient stoic philosophy to deliver an empowering treaty on how to perceive, act, and think about obstacles -and life-.

serenity prayer from the obstacle is the way

Bullet Summary

  • Look at obstacles positively and coolly: they’re an opportunity
  • Act on obstacles swiftly. No complaints, no regrets: just effective and persistent action
  • Be serene with whatever result. And move on. Positively and coolly


About The Author: Ryan Holiday is a former marketer and self-styled “media manipulator“.
But he’s also a top-notch, down-to-earth philosopher and a best-selling author.
Holiday has also been of the main influences in reclaiming and rediscovering ancient -yet also very actual- stoic philosophy.


The Obstacle Is The Way can be divided into three parts”

  1. Perception (how to perceive the obstacle)
  2. Action (how to deal with the action)
  3. Will (how to deal with intractable obstacles).

Part 1 – Perception

Chapter 1: Discipline of Perception

Perception is how we see and understand the world around us. How you perceive the world can be a strength or a weakness for you.

When first faced with an obstacle do the following:

  • Stay objective
  • Control emotions and keep calm
  • Choose to see the Positive
  • See things in perspective
  • Revert to the present moment
  • Focus on what you control

Seeing opportunities in obstacles does not come naturally: it’s a skill and an attitude you must train with self-discipline.

Chapter 2: Perspective: Your Power

The event, the obstacle, is neither good nor bad in itself.
It just is.

There are the event and the story we tell ourselves about what it means. It can be positive, negative, or there can be no story at all.

What if you were to consciously choose to tell yourself a positive story about the event?
Or what if you could choose an empowering perspective, and let your actions and emotions follow accordingly?

Because you can.

And that’s the power of perception.

Chapter 3: Steady Nerves and Control Emotions

Perception is everything, and if your nerves hold, nothing really happened.

When panic rears its ugly head, say “no thank you, I can’t afford to panic”, and go back to focusing on what you can control.

Ask yourself this:

Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, and straightforwardness?

Then get back to work.

Calm and collected, ready and prepared to throw your best at it.

Chapter 4: Practice Objectivity

Everything’s always so crystal clear and simple when you’re giving advice to other people, right?

Well, why don’t you do yourself a favor and use the same objectivity with yourself.

Do yourself a favor and pretend it’s not happening to you.

Chapter 5: Is It Up to You?

You only focus on what matters: all that you can control.

Your emotions, attitude, actions, perspective, decision, determination… These are all up to you.
These are the playing field, where you do whatever you need to.

All the rest, all the things you can’t control, are the rules of the game.
Don’t waste time and emotions on them.

Chapter 6: Live In the Present Moment

It doesn’t matter whether you’re in a growing economy or shrinking one, a good job market or a bad one, or your obstacle looms huge.

What matters is that right now is right now.

The implications of our obstacles are theoretical.
What will happen after, how better it was before the obstacle… All useless. They’re in the past and the future. We live in the moment. And the moment you embrace that, the easier the obstacle.

The Obstacle Is The Way discusses also entrepreneurial mentality and how entrepreneurs live in the present.
They are like animals with no time and ability to think about how things should be or how they’d prefer them to be. They just live and act in the present.

Chapter 7: Think Differently

Your perception will determine what you are capable or not capable of doing. And if you believe in the obstacle more than you believe in your goal, which one do you think is most likely to manifest?

So be open, to questions, but don’t let events and naysayers get to you.

Chapter 8: Finding the Opportunity

It’s common for people to have survived adversity or have faced major injuries to bounce back better than before. Some times physically, some other times emotionally.

“That which doesn’t kill me makes me stronger” is a fact and it has a name: Post-traumatic growth.

Chapter 9: Prepare to Act

Now that you know how important it is to steady your nerve and look at the positives, it’s time to act.

Part 2 – Action

Action is common, the right action is not. Your action must be directed, unrelenting and focused.

Chapter 10: The Discipline of Action

We’ve all been too busy, overwhelmed, tired, stressed. An then went out partying or slept, or did nothing.

It makes you feel better to pretend and ignore. But it isn’t helping you. You’ve got to act. Starting from now.

It doesn’t matter what happens to you or where you come from. It matters what you do with what happens and with what you have. And the only way you’ll do something spectacular is by using it all to your advantage.

Chapter 12: Get Moving

Whether you feel ready or not, however, the conditions, get moving.

Chapter 13: Practice Persistence

The people around you have already begun their chorus of doubts, excuses and dejection.
But you ain’t buying it.
You look at the problem dead on and say, as Margaret Thatcher famously did: “You turn if you want to. The lady’s not for turning.”

Too many people believe in the romanticized, yet painfully wrong idea, that great victories come from a flash of insight.
Like Thomas Edison.
No, it was the slow and constant pressure, from all directions, the elimination of hundreds more promising options, that slowly moved the solution to the top of the pile.

The genius, the real genius, was their doggedness, grit and staying power.

And that’s the message you gotta send to the world and to yourself: resistance is futile.

The genius was unity of purpose, deafness to doubt, and the desire to stay at it

Chapter 14: Iterate

Listen to the feedback you get from actions.
Doing so in an open, constructive way, is a key element in overturning obstacles.

That feedback is the instruction you need to reach your goal. That’s your road map to success: by showing you where not to go, your path to victory becomes clearer and clearer.

Failure shows us the way—by showing us what isn’t the way.

Chapter 15: Follow the Process

Huge obstacle?
The Obstacle Is The Way teaches us you don’t look at it like it’s a monolithic giant.
You break it into smaller units. And do what you need to do right now, do it well, and then move on to the next.

Follow the process, not the prize.

As they say, a journey of a thousand miles starts with a step.
And the step after, and after that. Focus on waking well, not on what might happen after the curve.
Excellence is a matter of step-by-step.
And soon you’ll be at the destination before you realize it.

Chapter 16: Do Your Job, Do It Right

Everything you do matters, everything is a chance to do and be your best. Whether that’s making smoothies or bar-tending as you save money for your dream.

I just gotta quote Ryan Holiday here as I love that part: Only self-absorbed assholes think they are too good for whatever their current station requires.

We will be and do many things in our life. Some are prestigious, some won’t be, but none are beneath us. Whatever we face, our job is to respond with hard work, honesty and helping others as best as we can. Wherever you are, you owe it to yourself and to the world to do it well. And when action is our priority, vanity falls away.

When action is our priority, vanity falls away.

Chapter 17: What’s Right is What Works

Do the best with what you’ve got.

That’s it.
Progress is your goal, not perfection.

Not that you don’t aim high, but you start thinking like a radical pragmatist: ambitious, aggressive, and even rooted in ideals, but also practical and grounded on the possible.
Because real artists ship.

Don’t think small, but keep in mind the difference between the critical and the extra.

Chapter 18: In Praise of the Flank Attack

Outnumbered, low on money, encircled by powerful competitors… These don’t have to be disadvantaged.

they can be your blessing in disguise. You got little chances head-to-head, so you’re forced to be creative and more efficient. And to finally put your ego aside.
People or companies who have the size advantage are resting on their laurels. They were able to coast for a long time on size and brute force. And that worked very well for them… Until it doesn’t anymore.
Until they met you.

Now you outflank them with swift action, outmaneuver them with speed, or pitch them one against the other.

Remember, a castle can be a scary and impenetrable fortress, or it can be a prison when surrounded.

Chapter 18: Channel Your Energy

Use all the emotions you get.

Our actions can become stronger when loose and bold. So take your frustration, and instead of giving in, use it to power your actions. Now you got physical looseness with mental mastery, and that’s powerful.

And you don’t disdain to work around the rules.
While others obsess with the rules, you’re subtly undermining them and subverting them to your advantage.

You are an unstoppable force, you’re a tide: slow and steady, there’s nowhere to run for your opponent.
External factors will influence the path, but not the direction: onward and upward.

Chapter 19: Seize The Offensive

In many battles, as in life, you will often reach a point of mutual exhaustion.

Two opposing forces will often reach a point of mutual exhaustion.
It’s the one who rises the next morning after a long day of fighting and rallies, instead of retreating who will carry victory home.

The obstacle is now your chance of winning.

Chapter 20: Prepare for None of It to Work

We can do a lot, but we can’t control the whole world around us. We might even fail.

Don’t let it get to you, your aim is to do your best. Not the impossible, but nothing less than your best.

And when you just can’t get through, here comes another opportunity: to learn and practice new virtues, even if that is only acceptance or humility.

You know the kind of person who throws at it everything he’s got and whatever the result, he is ready to accept it instantly and move on?

Is it you?

Because it can be.

Part 3 – Will

What is will?

Will is our internal power.
Will can never be affected by the outside world. When all action fails, will is our final trump card.

Chapter 21: The Discipline of Will

Some people think the Will is how badly we want something.

But that’s a weakness misguided by ambition. And it won’t serve you well under the biggest of obstacles.
Real Will is quiet humility, resilience, and flexibility.

Will is your ability to accept whatever happens. And be at peace with it. Will is wisdom.

Will is what prepares you to face anything you can face in an inherently unpredictable world.
Will is what keeps you going matter what’s happening around you.
Will is what allows you to stay calm and collected when everyone else loses their heads.

Chapter 22: Build Your Inner Citadel

Nobody is born a gladiator. Getting great at anything takes practice: you build your own Citadel, brick by brick.

Being great with adversity and cultivating Will is no different.

Chapter 23: Anticipation (Thinking Negatively)

Your world is ruled by external factors outside your control.

You’ll be vilified, threatened, bullied, lied to, and taken advantage of. You can’t be surprised every time it happens or it’ll make you miserable.

Be prepared for it instead -The Power Moves is here to for that-.

That’s anticipation called anticipation, and it’s both mental and practical.

Thanks to the anticipation you understand the range of potential outcomes and you can accommodate yourself to any of them.
You even understand it could go all wrong, and you’re OK with it. And now you can get back to work.

Chapter 24: The Art of Acquiescence

If someone took traffic signals personally, we would judge them as insane.

Yet that is exactly what life is telling us when faced with an obstacle.

It tells us the way is blocked and you need a detour. No arguing, no depression, you simply accept it.
Take people and events as they come and move around them: it’s only a bump along your road.

Ryan Holiday cites Eisenhower when he said:

Everything we could think of has been done, the troops are fit and everybody is doing his best. The answer is in the lap of the gods.

And he explains those were not the kind of men to just “hope for the best”, but at the end of the day, they understood that what happened would happen, and they’d go from there.

The answer is in the lap of the gods.

Chapter 25: Love Everything That Happens: Amor Fati

After you accept that some bad things will likely happen and it might be outside your control, here is the big one: Love whatever happens to you and face it with unfailing cheerfulness.

We don’t get to choose what happens to us, but we can always choose how we feel about it.
And why would you choose to feel anything but good about it? Don’t look back at your expectations, don’t think you thought it was going to be different. Face forward, and put a smug little grin.

We don’t get to choose what happens to us, but we can always choose how we feel about it.

Chapter 26: Perseverance

Perseverance is more than persisting at your problem.

Persistence is a matter of action, dependent on energy. Perseverance is a matter of Will, and it comes with endurance.
They work in conjunction.

Perseverance is a long game. Not just round 1. But round 2. and every round after.
It’s a belief that, eventually, somehow, you’ll get there.

Chapter 26: Something Bigger Than Yourself

Stop thinking of yourself all the time, and putting “I” in front of all the events. “I did very well but..”, “I deserve better than this..”.

No wonder you take losses so personally!

And stop pretending what you’re going through is somehow special or unfair.
Hundreds and thousands before you felt the same and had the same thoughts.
They had no idea that you would exist, and a century from now, someone will be in your exact same position.
Embrace the power of being part of a larger whole, it’s an exhilarating thought.

And do something helpful, think instead: if I can’t solve it for myself, how can I at least make it better for others?

This new shift in perception will immediately shift your thinking into a new gear. All of a sudden you’re thinking like a leader, and you’re a person who takes care of others.

Be strong for others, and it will make you stronger.

Chapter 27: Meditate on Your Mortality

No matter who you are or what your plans are, someone would kill you for a few dollars or a fix of heroin.
Or a car can hit you in an intersection and that’s it. It will be all over.

Today, tomorrow, or someday soon.

Or take the cliché question to ask:
“What would I change about my life if the doctor told me I had cancer”? After our answer, we inevitably comfort ourselves with the same insidious lie: “Well, thank God I don’t have cancer”.

But we do!
Our destinies are all already written.

And it’s not depressing. It’s invigorating. And reminding ourselves will help us treat our time and life as a beautiful gift (also read: how to leverage mortality for life).

It will also help create some badly needed urgency when we need to.

Instead of denying—or worse, fearing—our mortality, we can embrace it.

Chapter 28: Prepare to Start Again

Just when think you’ve successfully overcome an obstacle, another one comes along.

That’s how it is. And that’s what keeps life interesting. Life is a process of breaking through obstacles, learning, and growing along the way.
And, as you’re starting to adopt this mindset, that’s what creates opportunities.

One more obstacle and a bit more of the competition give up.
One more, and it’s just a few of you left.
One more and one more, until you’re the only one left: the best version of you.

the obstacle is the way book cover

Practical Applications

The Obstacle Is The Way” is the ultimate problem-solving book because it deals with mindsets.

Live, practice and internalize these 3 mindsets and you’ll reach new heights:

  • Looking at the obstacle mindset

You will look at the problem as an opportunity. Ask yourself “what can I learn”, and “how can it make me a better person”. Welcome adversities as a test and a chance to grow. No regrets, not what ifs. Only the present. And you will stay calm and collected.

  • Dealing with the obstacle mindset

You will do your best no matter what. Not the impossible, just your damn best. You will look at all possibilities with a never give up mentality. Piece by piece, you can be slowed down but not stopped. You’re an unstoppable force indeed. And you appreciate the struggle, in itself, as a welcome occasion for you to prove yourself.

  • Unsolvable obstacles mindset

With the first two mindsets of The Obstacle Is The Way you will forge ahead like never before.
But even when you’ll fail, you are calm and serene: this is an opportunity for you to wholly change direction, regroup or practice acceptance. You’ve done your best anyway, you don’t have regrets. What’s next.


The Obstacle Is The Way is a monument to the human spirit and ingenuity. It’s a masterpiece of empowering mindsets, applied philosophy and beautifully crafted, uplifting poetry.

Here are a few further comments for you:

Grateful for adversities
It is true that your most glorious moments come after searing defeats. Or when you snatched victory from the jaws of defeat. But also when you don’t win immediately, your adversities can make you a better person if you let them to.
I am grateful for many of my darkest days. I did use many of them to become a better person. And I am so proud of that. You can be too.

Entrepreneurial mentality
The Obstacle Is The Way expands also on entrepreneurial mentality. Ryan Holiday talks about how most of us have been taught of thinking “realistically” and how that’s a huge disadvantage for building a business.

Get the full book on Amazon.

I leave you with one last quote:

See things for what they are.
Do what we can.
Endure and bear what we must.

What blocked the path now is a path.
What once impeded action advances action.
The Obstacle is the Way.
Marcus Aurelius

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